DE69625238T2 - Alpha,beta-gesättigte und -ungesättigte 3-aryl-5-aminomethyl-butyrolactone antibakterielle mittel - Google Patents
Alpha,beta-gesättigte und -ungesättigte 3-aryl-5-aminomethyl-butyrolactone antibakterielle mittelInfo
- Publication number
- DE69625238T2 DE69625238T2 DE69625238T DE69625238T DE69625238T2 DE 69625238 T2 DE69625238 T2 DE 69625238T2 DE 69625238 T DE69625238 T DE 69625238T DE 69625238 T DE69625238 T DE 69625238T DE 69625238 T2 DE69625238 T2 DE 69625238T2
- Authority
- DE
- Germany
- Prior art keywords
- xiii
- oxo
- spp
- bromophenyl
- furanyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000003242 anti bacterial agent Substances 0.000 title abstract description 5
- 229920006395 saturated elastomer Polymers 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 7
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001540 azides Chemical class 0.000 claims description 5
- XPZXLALPOLILDV-UHFFFAOYSA-N n-[[4-bromo-4-(4-bromophenyl)-5-oxooxolan-2-yl]methyl]acetamide Chemical compound O=C1OC(CNC(=O)C)CC1(Br)C1=CC=C(Br)C=C1 XPZXLALPOLILDV-UHFFFAOYSA-N 0.000 claims description 5
- OAYFVVCIJWPGAQ-UHFFFAOYSA-N 2-(4-bromophenyl)pent-4-enoic acid Chemical compound C=CCC(C(=O)O)C1=CC=C(Br)C=C1 OAYFVVCIJWPGAQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002243 precursor Substances 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- NJAXPGKEUFXWDY-UHFFFAOYSA-N n-[[4-[4-(4-methoxy-5-oxocyclohepta-1,3,6-trien-1-yl)phenyl]-5-oxo-2h-furan-2-yl]methyl]acetamide Chemical compound C1=CC(=O)C(OC)=CC=C1C1=CC=C(C=2C(OC(CNC(C)=O)C=2)=O)C=C1 NJAXPGKEUFXWDY-UHFFFAOYSA-N 0.000 claims description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
- STAVSZYYVQALSW-UHFFFAOYSA-N n-[[4-(4-bromophenyl)-5-oxooxolan-2-yl]methyl]acetamide Chemical compound O=C1OC(CNC(=O)C)CC1C1=CC=C(Br)C=C1 STAVSZYYVQALSW-UHFFFAOYSA-N 0.000 claims description 2
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 claims description 2
- 229910001948 sodium oxide Inorganic materials 0.000 claims description 2
- BQAPBGFSAOOMQF-UHFFFAOYSA-N 3-(4-bromophenyl)-5-(iodomethyl)oxolan-2-one Chemical compound C1=CC(Br)=CC=C1C1C(=O)OC(CI)C1 BQAPBGFSAOOMQF-UHFFFAOYSA-N 0.000 claims 3
- NVXSACKMSVLEEX-UHFFFAOYSA-N 5-(azidomethyl)-3-(4-bromophenyl)oxolan-2-one Chemical compound Brc1ccc(cc1)C1CC(CN=[N+]=[N-])OC1=O NVXSACKMSVLEEX-UHFFFAOYSA-N 0.000 claims 1
- -1 troponyl Chemical group 0.000 abstract description 8
- 241001148536 Bacteroides sp. Species 0.000 abstract description 2
- 241001112696 Clostridia Species 0.000 abstract description 2
- 241000186359 Mycobacterium Species 0.000 abstract description 2
- 241000186367 Mycobacterium avium Species 0.000 abstract description 2
- 241000187479 Mycobacterium tuberculosis Species 0.000 abstract description 2
- 241000204031 Mycoplasma Species 0.000 abstract description 2
- 241000295644 Staphylococcaceae Species 0.000 abstract description 2
- 241001148470 aerobic bacillus Species 0.000 abstract description 2
- 244000052769 pathogen Species 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- 241000894007 species Species 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 abstract 2
- 150000003457 sulfones Chemical class 0.000 abstract 2
- 150000003462 sulfoxides Chemical class 0.000 abstract 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical class O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 abstract 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000002785 azepinyl group Chemical group 0.000 abstract 1
- 125000002393 azetidinyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 abstract 1
- 125000002757 morpholinyl group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004193 piperazinyl group Chemical group 0.000 abstract 1
- 125000003386 piperidinyl group Chemical group 0.000 abstract 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 1
- 229940124530 sulfonamide Drugs 0.000 abstract 1
- 150000003456 sulfonamides Chemical class 0.000 abstract 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 abstract 1
- 125000001984 thiazolidinyl group Chemical group 0.000 abstract 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000007858 starting material Substances 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 6
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000007832 Na2SO4 Substances 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000003115 biocidal effect Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 229960002317 succinimide Drugs 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 150000001499 aryl bromides Chemical class 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- GOUILHYTHSOMQJ-UHFFFAOYSA-N gamma-butenolide Natural products CCC1OC(=O)C=C1 GOUILHYTHSOMQJ-UHFFFAOYSA-N 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UDHQYCHTORTPRF-UHFFFAOYSA-N 2-phenylcyclohepta-2,4,6-trien-1-one Chemical group O=C1C=CC=CC=C1C1=CC=CC=C1 UDHQYCHTORTPRF-UHFFFAOYSA-N 0.000 description 1
- QOWSWEBLNVACCL-UHFFFAOYSA-N 4-Bromophenyl acetate Chemical compound OC(=O)CC1=CC=C(Br)C=C1 QOWSWEBLNVACCL-UHFFFAOYSA-N 0.000 description 1
- LHQQWHDQEYLWQA-UHFFFAOYSA-N C(=O)(NCC1C=C(C2=CC=C(Br)C=C2)C(=O)O1)C Chemical compound C(=O)(NCC1C=C(C2=CC=C(Br)C=C2)C(=O)O1)C LHQQWHDQEYLWQA-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
- VVBXKASDRZXWON-UHFFFAOYSA-N N=[PH3] Chemical compound N=[PH3] VVBXKASDRZXWON-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 108010059993 Vancomycin Proteins 0.000 description 1
- 241000748245 Villanova Species 0.000 description 1
- 238000002814 agar dilution Methods 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 238000009635 antibiotic susceptibility testing Methods 0.000 description 1
- 150000001543 aryl boronic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- POXUJOYUVLWPQN-ZDUSSCGKSA-N n-[[(5s)-3-(4-acetylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(C(C)=O)C=C1 POXUJOYUVLWPQN-ZDUSSCGKSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000010651 palladium-catalyzed cross coupling reaction Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/58—One oxygen atom, e.g. butenolide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/28—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US383795P | 1995-09-15 | 1995-09-15 | |
| PCT/US1996/013726 WO1997010235A1 (fr) | 1995-09-15 | 1996-09-05 | AGENTS ANTIBACTERIENS A BASE DE 5-AMIDOMETHYLE, 3-ARYLE BUTYROLACTONE α, β SATURE ET INSATURE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69625238D1 DE69625238D1 (de) | 2003-01-16 |
| DE69625238T2 true DE69625238T2 (de) | 2003-07-24 |
Family
ID=21707825
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69625238T Expired - Fee Related DE69625238T2 (de) | 1995-09-15 | 1996-09-05 | Alpha,beta-gesättigte und -ungesättigte 3-aryl-5-aminomethyl-butyrolactone antibakterielle mittel |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5708169A (fr) |
| EP (1) | EP0863890B1 (fr) |
| JP (1) | JPH11511467A (fr) |
| AT (1) | ATE229014T1 (fr) |
| AU (1) | AU6902096A (fr) |
| DE (1) | DE69625238T2 (fr) |
| DK (1) | DK0863890T3 (fr) |
| ES (1) | ES2185800T3 (fr) |
| PT (1) | PT863890E (fr) |
| WO (1) | WO1997010235A1 (fr) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9601666D0 (en) * | 1996-01-27 | 1996-03-27 | Zeneca Ltd | Chemical compounds |
| GB9702213D0 (en) | 1996-02-24 | 1997-03-26 | Zeneca Ltd | Chemical compounds |
| GB9609919D0 (en) * | 1996-05-11 | 1996-07-17 | Zeneca Ltd | Chemical compounds |
| GB9717807D0 (en) * | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
| GB9717804D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
| GB9725244D0 (en) | 1997-11-29 | 1998-01-28 | Zeneca Ltd | Chemical compounds |
| TR200003595T2 (tr) * | 1998-06-05 | 2001-07-23 | Astrazeneca Ab | Kimyasal bileşikler |
| TW572757B (en) * | 1998-08-24 | 2004-01-21 | Bristol Myers Squibb Co | Novel isoxazolinone antibacterial agents |
| US6420349B1 (en) | 1998-08-24 | 2002-07-16 | Bristol-Myers Squibb Company | Isoxazolinone antibacterial agents |
| EP1191948A2 (fr) * | 1999-06-11 | 2002-04-03 | Neorx Corporation | Complexe a forte dose de radionucleides destine a la suppression de la moelle osseuse |
| US7094885B2 (en) * | 1999-07-11 | 2006-08-22 | Neorx Corporation | Skeletal-targeted radiation to treat bone-associated pathologies |
| GB9928568D0 (en) | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical compounds |
| GB0009803D0 (en) * | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| US6465456B2 (en) | 2000-06-29 | 2002-10-15 | Bristol-Myers Squibb Company | Isoxazolinone antibacterial agents |
| EP1390081A2 (fr) * | 2001-01-08 | 2004-02-25 | Neorx Corporation | Composes, compositions et methodes therapeutiques et diagnostiques |
| US7045116B2 (en) | 2001-12-13 | 2006-05-16 | Dow Global Technologies Inc. | Treatment of osteomyelitis with radiopharmaceuticals |
| BR0316483A (pt) | 2002-11-21 | 2005-10-11 | Upjohn Co | Derivados de n-(4-(piperazin-1-il)-fenil-2-oxazolidinona-5-carboxami da e compostos relacionados como agentes antibacterianos |
| WO2013086201A1 (fr) | 2011-12-06 | 2013-06-13 | Dowd Scot E | Dosages universels ou à large plage et procédé de diagnostic spécifique d'échantillons à marquages multiples à l'aide d'un séquençage non optique |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3446821A (en) * | 1964-09-17 | 1969-05-27 | Squibb & Sons Inc | Intermediates useful in preparation of butenolides and process therefor |
| US3331837A (en) * | 1964-10-30 | 1967-07-18 | Schering Ag | alpha, beta-unsaturated gamma-lactone compounds and process for the production of same |
| US3496187A (en) * | 1967-03-20 | 1970-02-17 | American Home Prod | N-(heterocyclyl)aconamides |
| US3576010A (en) * | 1967-06-16 | 1971-04-20 | Monsanto Co | Substituted anilino halogenated furanones |
| US3444178A (en) * | 1967-06-16 | 1969-05-13 | Monsanto Co | Certain halogenated 2-(2-thiazolyl) aminofuran-5-ones |
| US3647656A (en) * | 1969-04-09 | 1972-03-07 | Ibm | Method of preparing alpha substituted beta gamma unsaturated lactones from alkoxyfurans |
| JPS495961A (fr) * | 1972-05-10 | 1974-01-19 | ||
| FR2456097A1 (fr) * | 1979-05-07 | 1980-12-05 | Delalande Sa | Nouveaux derives de la 5 h-furanone-2 et de la 3 h-dihydrofuranone-2, leur procede de preparation et leur application en therapeutique |
| JPS5746975A (en) * | 1980-09-04 | 1982-03-17 | Sanwa Chem:Kk | Preparation of alpha- or beta-substituted -deltaalpha,beta-or deltabeta-,gamma-butenolide |
| JPS5932467B2 (ja) * | 1981-03-04 | 1984-08-09 | 理化学研究所 | ５員環不飽和ラクトンの製造方法 |
| JPS5932466B2 (ja) * | 1981-03-04 | 1984-08-09 | 理化学研究所 | ５員環不飽和ラクトンの製造方法 |
| JPS5852995B2 (ja) * | 1981-09-28 | 1983-11-26 | 武田薬品工業株式会社 | フルフラ−ル誘導体の製造法 |
| JPS59164787A (ja) * | 1983-03-09 | 1984-09-17 | Rikagaku Kenkyusho | ５員環不飽和ラクトンの製造方法 |
| GB8401149D0 (en) * | 1984-01-17 | 1984-02-22 | Fujisawa Pharmaceutical Co | Furanone derivatives |
| JPS6393774A (ja) * | 1986-10-09 | 1988-04-25 | Sumitomo Chem Co Ltd | ４−アミノ−２（５ｈ）−フラノン誘導体の製造法 |
| JP2765001B2 (ja) * | 1988-02-23 | 1998-06-11 | 武田薬品工業株式会社 | プロテアーゼ阻害剤 |
| JPH01313476A (ja) * | 1988-06-13 | 1989-12-18 | Kao Corp | ３−ｏ−アシル−５，６−ｏ−ベンジリデンアスコルビン酸 |
| JPH05294952A (ja) * | 1992-04-16 | 1993-11-09 | Wakamoto Pharmaceut Co Ltd | 抗生物質ｗａｐ−４０６８および誘導体ならびにそれらの製造法 |
| ATE161833T1 (de) * | 1992-12-08 | 1998-01-15 | Upjohn Co | Durch eine tropon gruppe substituierte phenyloxazolidinone-derivate als antibakterielles mittel |
| MY115155A (en) * | 1993-09-09 | 2003-04-30 | Upjohn Co | Substituted oxazine and thiazine oxazolidinone antimicrobials. |
-
1996
- 1996-09-05 DK DK96929740T patent/DK0863890T3/da active
- 1996-09-05 WO PCT/US1996/013726 patent/WO1997010235A1/fr active IP Right Grant
- 1996-09-05 JP JP9511972A patent/JPH11511467A/ja not_active Withdrawn
- 1996-09-05 US US08/708,765 patent/US5708169A/en not_active Expired - Fee Related
- 1996-09-05 AT AT96929740T patent/ATE229014T1/de not_active IP Right Cessation
- 1996-09-05 AU AU69020/96A patent/AU6902096A/en not_active Abandoned
- 1996-09-05 EP EP96929740A patent/EP0863890B1/fr not_active Expired - Lifetime
- 1996-09-05 ES ES96929740T patent/ES2185800T3/es not_active Expired - Lifetime
- 1996-09-05 DE DE69625238T patent/DE69625238T2/de not_active Expired - Fee Related
- 1996-09-05 PT PT96929740T patent/PT863890E/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU6902096A (en) | 1997-04-01 |
| WO1997010235A1 (fr) | 1997-03-20 |
| EP0863890A1 (fr) | 1998-09-16 |
| US5708169A (en) | 1998-01-13 |
| PT863890E (pt) | 2003-04-30 |
| DE69625238D1 (de) | 2003-01-16 |
| ES2185800T3 (es) | 2003-05-01 |
| DK0863890T3 (da) | 2003-03-24 |
| EP0863890B1 (fr) | 2002-12-04 |
| ATE229014T1 (de) | 2002-12-15 |
| JPH11511467A (ja) | 1999-10-05 |
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